Skip to main content
A forest with autumn foliage reflecting in a calm lake.

Stratton Vacations from $839

Book a Hotel + Flight or Car together to unlock savings

The Latest Stratton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Front of property - evening/night
    Oct 15 - Oct 20

    Golden Stage Inn B&B + Flight

    Cavendish
    5 nights
    3.5 star property
    10/10 - Exceptional (45 reviews)
    "Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!"
    Reviewed July 6, 2026
    Roundtrip • Minneapolis (MSP) - Rutland (RUT)
    MSP - BOS • 1 stop BOS - MSP • 1 stop
    $1,053
    $839
    per traveler
    found 1 day ago
    Golden Stage Inn B&B
  • Breakfast and dinner served
    Sep 8 - Sep 14

    The Mountain Inn at Killington + Flight

    Killington
    6 nights
    2.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    "The staff was excellent; helpful, cheery, and knowledgeable. The place is a bit old but is very clean. The breakfast was good and the breakfast sandwiches excellent."
    Reviewed August 3, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - ORD • 1 stop
    $1,307
    $1,098
    per traveler
    found 1 day ago
    The Mountain Inn at Killington
  • Exterior
    Oct 7 - Oct 10

    Holiday Inn Club Vacations Mount Ascutney Resort by IHG + Flight

    Brownsville
    3 nights
    3.0 star property
    9.0/10 - Wonderful (862 reviews)
    Roundtrip • New York (EWR) - Rutland (RUT)
    EWR - RUT • 1 stop RUT - EWR • 1 stop
    $1,074
    $904
    per traveler
    found 1 day ago
    Holiday Inn Club Vacations Mount Ascutney Resort by IHG
  • Lobby
    Sep 8 - Sep 14

    Days Inn by Wyndham Rutland/Killington Area + Flight

    Rutland
    6 nights
    2.5 star property
    6.8/10 - (1,004 reviews)
    "Just a quick trip up for a work event, easy to check in, pool is open late so everyone an relax even after a late check in. So many restaurants to choose from!"
    Reviewed August 2, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - ORD • 1 stop
    $1,155
    $978
    per traveler
    found 1 day ago
    Days Inn by Wyndham Rutland/Killington Area
  • Lounge
    Sep 8 - Sep 14

    Greenbrier Inn + Flight

    Killington
    6 nights
    2.0 star property
    9.4/10 - Exceptional (686 reviews)
    "Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony."
    Reviewed August 3, 2026
    Roundtrip • Chicago (CHI) - Rutland (RUT)
    ORD - RUT • 1 stop RUT - ORD • 1 stop
    $1,201
    $1,021
    per traveler
    found 1 day ago
    Greenbrier Inn

Discover the most popular places to visit in Stratton

Stratton Mountain Resort

9.2/10 (365 reviews)
Stratton Mountain Resort offers 99 trails across 2,003 feet of vertical terrain for winter sports. Enjoy year-round adventures from skiing to golf and mountain biking in southern Vermont's premier outdoor playground.

Stratton Hotel Deals

WiFi (free), bed sheets

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
2.5 mi from Stratton
7.6 out of 10, Good, (1,002 reviews)
$138 nightly
The price is $152
Sep 2 - Sep 3
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Stratton

Frequently Asked Questions

How much does a Stratton vacation package cost?

You can grab a vacation package to this popular destination from $839 on Expedia. However, how much your vacation to Stratton costs will depend on factors like the length of stay, hotel choice and season.

What are the cheapest months to go to Stratton?

If you're hoping to snag a cheap Stratton vacation package, consider planning a trip in May, June and August. You'll usually find lower prices on flights and accommodations during these months — perfect for budget-conscious travelers.

How many days is enough for Stratton?

The ideal length of your Stratton vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to check out all the main sights and explore some hidden spots along the way.

How to find the best Stratton package deals?

Finding a cheap Stratton package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Stratton package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.

Is it cheaper to book a Stratton vacation as a package?

Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Stratton vacation by choosing your favorite type of stay, airline and car class.

When to book a vacation package to Stratton?

If you're considering a spur-of-the-moment Stratton adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.

How to plan a trip to Stratton?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Stratton.
  2. Set your budget: Consider costs such as flights, transportation and food when working out how much to set aside for your trip to Stratton. Then, select a hotel that fits your budget, whether that's a wallet-friendly stay or a deluxe getaway.
  3. Use Expedia's trip planning tool to discover Stratton: Research every aspect of your trip to Stratton with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Stratton. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Stratton vacation package that brings all your bookings together.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the best Stratton has to offer. Find all the exciting things to do in Stratton with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Stratton vacation packages?

If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Stratton trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

Book with confidence

Things to do in and around Stratton

Stratton, Vermont, is a fantastic destination for ski and adventure enthusiasts. Popular activities include skiing at the renowned Stratton ski resort and enjoying the Stratton Golf School during warmer months. For a thrilling experience, consider snowmobile tours or plan a day trip to explore the beautiful surroundings. An activity guide is available to help you make the most of your vacation in this picturesque area.

Shopping

For a great shopping experience in Stratton, visit Margie's Muse Handweaving & Gallery, just 5 miles away, for unique gifts. If you're up for a drive, check out the Manchester Designer Outlets, located 9 miles away, or the West River Farmers Market, 11 miles away, for local goodies.

Recreation

Stratton Mountain Golf Course offers a stunning outdoor experience with breathtaking views and challenging holes, perfect for golf enthusiasts. For relaxation, Dana L. Thompson Memorial Park provides a peaceful atmosphere with picnic spots and walking trails, while the Dorset Playhouse enriches your visit with captivating performances and cultural experiences.

Adventure

At Stratton Mountain Resort, enjoy thrilling skiing and snowboarding on varied terrain, surrounded by breathtaking mountain views. Take a ride on the American Express Ski Lift for easy access to the slopes. For a scenic experience, hop on the Stratton Mountain Summit Gondola and soak in the stunning vistas.

Nightlife

In Stratton, Vermont, enjoy a cozy nightlife with local pubs and bars like the Green Door Pub and the Stratton Mountain Resort's nightlife offerings. Experience live music, craft beers, and a friendly atmosphere, perfect for unwinding after a day on the slopes.

Find the best attractions in and around Stratton

Stratton, Vermont is an ideal destination for ski and adventure lovers, offering a range of outdoor and cultural experiences. Explore the scenic Stratton Mountain Resort, take a ride on the Stratton Mountain Summit Gondola for breathtaking mountain views, and enjoy a round of golf at the Stratton Mountain Golf Course. With its beautiful national parks and rivers, Stratton promises unforgettable adventures for every traveler.

  • Stratton Mountain Resort: This premier ski resort offers thrilling winter sports and summer adventures amidst breathtaking mountain views. With diverse ski trails, snowboarding, and family-friendly activities, it’s perfect for outdoor enthusiasts seeking excitement and relaxation in a picturesque setting.
  • Green Mountain National Forest: Located 8 miles from Stratton, this national park is a haven for nature lovers, featuring stunning scenery, lush forests, and ample opportunities for hiking, camping, and wildlife observation. It’s an ideal spot for adventure seekers wanting to immerse themselves in Vermont’s natural beauty.
  • Golf Club at Equinox: Situated 9 miles away, this exquisite golf course offers a challenging layout and beautiful accommodations. Surrounded by stunning landscapes, it provides a perfect blend of relaxation and adventure for golf enthusiasts and nature lovers alike.

Best time to go to Stratton

The best time to visit Stratton can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Stratton falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Stratton falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

Tips to save on your trip to Stratton

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Stratton.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.